EP2441805B1 - Schwarze Disazofarbstoffe, ihre Herstellung sowie Verwendung - Google Patents
Schwarze Disazofarbstoffe, ihre Herstellung sowie Verwendung Download PDFInfo
- Publication number
- EP2441805B1 EP2441805B1 EP10187827.0A EP10187827A EP2441805B1 EP 2441805 B1 EP2441805 B1 EP 2441805B1 EP 10187827 A EP10187827 A EP 10187827A EP 2441805 B1 EP2441805 B1 EP 2441805B1
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- EP
- European Patent Office
- Prior art keywords
- group
- hydrogen atom
- carbon atoms
- sulphonic acid
- acid group
- Prior art date
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- 239000000975 dye Substances 0.000 title claims description 88
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 42
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 24
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- -1 sulphonyl group Chemical group 0.000 claims description 19
- 238000007641 inkjet printing Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000002560 nitrile group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000565 sulfonamide group Chemical group 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000007639 printing Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- ASDREVVGQFYRTH-UHFFFAOYSA-N 3-[[2-acetamido-4-[(4-amino-6-chloro-1,3,5-triazin-2-yl)amino]phenyl]diazenyl]naphthalene-1,5-disulfonic acid Chemical compound C=1C=C(N=NC=2C=C3C(=CC=CC3=C(C=2)S(O)(=O)=O)S(O)(=O)=O)C(NC(=O)C)=CC=1NC1=NC(N)=NC(Cl)=N1 ASDREVVGQFYRTH-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 239000001043 yellow dye Substances 0.000 claims description 4
- 239000010985 leather Substances 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 150000002641 lithium Chemical group 0.000 claims description 2
- 239000007783 nanoporous material Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 125000004436 sodium atom Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 claims 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 15
- 230000015556 catabolic process Effects 0.000 description 14
- 238000006731 degradation reaction Methods 0.000 description 14
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 10
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 10
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 8
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 description 3
- LCLMBELQCZQATE-UHFFFAOYSA-N 4-aminobenzene-1,2-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(S(O)(=O)=O)=C1 LCLMBELQCZQATE-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 0 *c1ccc(*=*c2c(*)c(C([C@](*=*c3ccccc3)C(N)=C3)O)c3c(N)c2)cc1 Chemical compound *c1ccc(*=*c2c(*)c(C([C@](*=*c3ccccc3)C(N)=C3)O)c3c(N)c2)cc1 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- FGHYCAHVTIVKDB-UHFFFAOYSA-N 2-amino-4-methyl-5-nitrobenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1[N+]([O-])=O FGHYCAHVTIVKDB-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000001454 recorded image Methods 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- GWAKFAUFNNPZFE-UHFFFAOYSA-K trisodium 2-[4-[(2-amino-4-oxidophenyl)diazenyl]anilino]-5-[(1-amino-8-oxido-7-phenyldiazenyl-3,6-disulfonaphthalen-2-yl)diazenyl]benzenesulfonate Chemical compound NC1=C(C(=CC2=CC(=C(C(=C12)O)N=NC1=CC=CC=C1)S(=O)(=O)[O-])S(=O)(=O)[O-])N=NC1=CC(=C(C=C1)NC1=CC=C(C=C1)N=NC1=C(C=C(C=C1)O)N)S(=O)(=O)[O-].[Na+].[Na+].[Na+] GWAKFAUFNNPZFE-UHFFFAOYSA-K 0.000 description 2
- XGGSABKVDMOUGH-UHFFFAOYSA-N 2-aminobenzene-1,3,5-trisulfonic acid Chemical compound NC1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C=C1S(O)(=O)=O XGGSABKVDMOUGH-UHFFFAOYSA-N 0.000 description 1
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 1
- VZLLZDZTQPBHAZ-UHFFFAOYSA-N 2-nitroaniline-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O VZLLZDZTQPBHAZ-UHFFFAOYSA-N 0.000 description 1
- SJCTXIKOXTUQHC-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl SJCTXIKOXTUQHC-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- PHRVJZNHPVJYOM-UHFFFAOYSA-N 5-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(N)C(S(O)(=O)=O)=C1 PHRVJZNHPVJYOM-UHFFFAOYSA-N 0.000 description 1
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 1
- AOMZHDJXSYHPKS-DROYEMJCSA-L Amido Black 10B Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(\N=N\C=3C=CC=CC=3)C(O)=C2C(N)=C1\N=N\C1=CC=C(N(=O)=O)C=C1 AOMZHDJXSYHPKS-DROYEMJCSA-L 0.000 description 1
- BUURMHBKUUZRFW-UHFFFAOYSA-N Cc(c(Cl)cc(S(O)(=O)=O)c1N)c1Cl Chemical compound Cc(c(Cl)cc(S(O)(=O)=O)c1N)c1Cl BUURMHBKUUZRFW-UHFFFAOYSA-N 0.000 description 1
- OTVUVZCOLDTZOY-UHFFFAOYSA-N Cc(c([N+]([O-])=O)c1S(O)(=O)=O)ccc1N Chemical compound Cc(c([N+]([O-])=O)c1S(O)(=O)=O)ccc1N OTVUVZCOLDTZOY-UHFFFAOYSA-N 0.000 description 1
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N Cc(cc1S(O)(=O)=O)ccc1N Chemical compound Cc(cc1S(O)(=O)=O)ccc1N LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- HFIYIRIMGZMCPC-UHFFFAOYSA-J chembl1326377 Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC(=CC=3)S(=O)(=O)CCOS([O-])(=O)=O)C(O)=C2C(N)=C1N=NC1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 HFIYIRIMGZMCPC-UHFFFAOYSA-J 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 230000005686 electrostatic field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004154 testing of material Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/025—Disazo dyes containing acid groups, e.g. -COOH, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
Definitions
- the invention relates to novel black disazo dyes, their salts, a method of their preparation and their use in dying and printing operations. It relates also to liquid dye preparations containing these dyes, in particular to aqueous recording fluids for ink jet printing and for writing utensils.
- Ink jet printing processes are essentially of two types:
- Recording sheets suitable for these printers need to absorb the recording liquids very rapidly, in particular during the printing of photo realistic images.
- Recording sheets particularly suitable for this purpose comprise nanoporous inorganic compounds, preferably oxides, such as aluminium oxides or silicon dioxide, or oxide/ hydroxides, such as aluminium oxide/hydroxides. These recording sheets are known as "nanoporous" recording sheets.
- Nanoporous recording sheets absorb the recording liquids very rapidly (in the microsecond range) by the action of the capillary forces of the nanoporous compounds.
- Polymer based recording sheets absorb the recording liquids more slowly (in the millisecond range) by swelling of the polymer.
- the black dyes used nowadays do not have all required properties, such as very high brilliance (saturation), a suitable hue, good light stability, good resistance against degradation by ozone, an excellent diffusion fastness. They have to penetrate into the recording sheet and should not show dye aggregation on the surface of the recording sheet ("bronzing") and they need to have an excellent solubility in the mainly aqueous recording liquid. is a widely used, commercially available black dye.
- Direct Black 168 Recording fluids for ink jet printing containing C.I. Direct Black 168 are described in patent applications WO93/24'330 , EP 0'885'940 and US 2002/0'121'219 . However, if used for dyeing paper or in recording fluids for ink jet printing, it is not soluble enough and it gives recorded images having insufficient water-durability, showing bronzing and a non-neutral hue on nanoporous media. It causes clogging of nozzles of the printing head due to deposition of dye. Direct Black 168 has to be used in a mixture with pacified C.I. Reactive Black 31 in order to provide blacks with a neutral hue. is also a widely used, commercially available black dye.
- This dye also has a bluish hue and cannot be used alone as a black dye in recording liquids for ink jet printing. is described in patent application US 2007/0'050'926 as being particularly suitable as a light-fast component in a black recording fluid for ink jet printing. However, its resistance against degradation by ozone is bad.
- the present invention refers to novel black disazo dyes of general formula (V) wherein
- dyes of general formula (V), wherein the sulpho group is in position ⁇ are particularly preferred.
- the invention does not only relate to pure black dyes of general formula (V), but also to mixtures of these dyes.
- the invention also relates to a method of preparation of the dyes of general formula (V) according to the invention, wherein, in a first step, an amine of general formula (XII) wherein R 1 , R 2 , R 3 , R 4 , and R 5 are as defined before, is diazotised in an aqueous inorganic acid medium at a temperature between -5° C and 15° C and coupled with the compound of formula (XIV) at an acidic to weakly acidic value of pH, and, in a second step, an amine of general formula (XV) wherein R 6 , R 7 , R 8 , R 9 and R 10 are as defined before, is diazotised in an inorganic acid medium at a temperature between -5° C and 15° C and coupled with the reaction product of step 1 at a weakly basic to basic value of pH.
- a first step an amine of general formula (XII) wherein R 1 , R 2 , R 3 , R 4 , and R 5 are as defined
- An acidic to weakly acidic value of pH means a value of pH situated between 1 and 4.
- a weakly basic to basic value of pH means a value of pH situated between 8 and 10.
- the compound of formula (XIV), wherein the sulpho group is in position ⁇ , is also known as K acid (4-amino-5-hydroxynaphthalene-1,7-disulphonic acid).
- the compound of formula (XIV), wherein the sulpho group is in position ⁇ , is also known as H acid (4-amino-5-hydroxynaphthalene-2,7-disulphonic acid).
- the invention does not only relate to pure black dyes of general formula (V), but also to mixtures of these dyes.
- the black disazo dyes of general formula (V) according to the invention are used for dying cellulose containing materials, paper, cotton, viscose, leather and wool to provide dyed materials with good water fastness and light stability.
- All methods well known in the textile and paper industries for dyeing with substantive dyes may be used, in particular for the bulk or surface treatment of sized or unsized paper.
- the dyes may also be used in the dyeing of yarns and piece goods of cotton, viscose and linen by the exhaustion process from a long liquor or in a continuous process.
- the invention furthermore relates to liquid dye preparations comprising at least one black disazo dye of general formula (V).
- liquid dye preparations comprising at least one black disazo dye of general formula (V).
- the use of such liquid dye preparations is particularly preferred for paper dyeing.
- Such stable, liquid, preferably aqueous, concentrated dye preparations may be obtained by using methods well known in the art, preferably by dissolving in suitable solvents.
- the possibility of preparation of such stable, aqueous, concentrated preparations in the course of dye synthesis itself, without intermediate isolation of the dye, for example after a desalting step by diafiltration of the reaction solution, is of particular advantage.
- the invention claims also a process for recording text and images on recording sheets and for dying and printing natural or synthetic fibre materials, nanoporous materials, leather and aluminium by applying thereto a black disazo dyes or a mixture of black disazo dyes according to the invention.
- the black disazo dye or the mixture of black disazo dyes of general formula (V) are excellent dyes for the preparation of black recording liquids for ink jet printing and for writing utensils.
- yellow dyes as for example C.I. Direct Yellow 86, C.I. Direct Yellow 98, C.I. Direct Yellow 132, C.I. Direct Yellow 142, C.I. Direct Yellow 173, C.I. Acid Yellow 23, C.I. Reactive Yellow 3, the hydrolysed derivative of C.I. Reactive Yellow 3, C.I. Yellow 85, the hydrolysed derivative of C.I. Yellow 85, C.I. Yellow 95 or the hydrolysed derivative of C.I. Yellow 95, may be added to the black disazo dyes of general formula (V) according to the invention, in order to obtain a neutral black hue of the printed recording liquids.
- V black disazo dyes of general formula (V) according to the invention
- the intermediate monoazo compound of formula (XVII) was prepared in the following way:
- the intermediate monoazo compound of formula (XVIII) was prepared in a similar way by using aniline-4-sulphonic acid (compound of general formula (XII)) in place of aniline-2,5-disulphonic acid and 4-amino-5-hydroxynaphthalene-2,7-disulphonic acid (H acid) in place of 4-amino-5-hydroxynaphthalene-1,7-disulphonic acid (K acid) of example 1a.
- aniline-4-sulphonic acid compound of general formula (XII)
- H acid 4-amino-5-hydroxynaphthalene-2,7-disulphonic acid
- K acid 4-amino-5-hydroxynaphthalene-1,7-disulphonic acid
- the dye (2) was salted out by the combined addition of sodium acetate and ethanol.
- the precipitated dye (2) was filtered off, washed with an ethanol/water mixture (2 : 1), dialysed be reverse osmosis, the water was removed by evaporation and dye (2) was dried.
- Dye (2) was obtained in a yield of 77 %.
- the monoazo compound of formula (XVIII) was used in place of the monoazo compound of formula (XVII) of example 2.
- 2-Aminobenzonitrile-3,5-disulphonic acid was prepared by reacting 2-aminobenzonitrile with 4 equivalents of sulphamic acid in N-methylpyrrolidone at a temperature of 110° C for 4 hours.
- Aniline-3,5-dicarboxylic acid was used in place of aniline-4,5-disulphonic acid of example 12.
- Aniline-2,4,6-trisulphonic acid was used in place of aniline-4,5-disulphonic acid example 7.
- H acid 4-Amino-5-hydroxynaphthalene-2,7-disulphonic acid
- K acid 4-amino-5-hydroxynaphthalene-1,7-disulphonic acid
- H acid 4-Amino-5-hydroxynaphthalene-2,7-disulphonic acid
- K acid 4-amino-5-hydroxynaphthalene-1,7-disulphonic acid
- the present invention is illustrated by the following examples using the disazo dyes (2) to (24) according to the invention and dyes representing the state of the art.
- 100 g of recording liquid were prepared by heating the necessary amount of dye (0.5 g to 1.0 g), ethylene glycol (0.6 g), propylene-1,2-glycol (0.3 g), 1-methyl-2-pyrrolidone (0.3 g), an aqueous solution (50 %) of Olin ® 10G (available from Arch Chemicals Inc., Norwalk, USA) (0.03 g), Surfinol ® 465 (available from Air Products and Chemicals Inc., Allentown, USA) (0.03 g) and a solution of the biocide Mergal ® K 10N (available from Riedel-de-Ha ⁇ n, Seelze, Germany) (0.01 g) together with water at a temperature of 50° C under stirring for approximately 1 hour.
- the resulting solution was cooled down to a temperature of 20° C, its value of pH was adjusted to 7.5 and the solution was passed through a Millipore ® filter of 0.5 ⁇ m pore diameter.
- the dye quantity was adjusted in such a way that the optical density of the printed image was similar for all dyes.
- the colour coordinates L*a*b* of the coloured square patches were measured with a spectrophotometer Spectrolino ® (available from Gretag Macbeth, Regensdorf, Switzerland) in reflection (illuminant D 65 ).
- Black dyes have a low value of C*.
- the printed samples were irradiated using a Weather-Ometer ® Ci35A (available from Atlas Material Testing Technology, Chicago, USA) with a 6500 W xenon lamp at a temperature of 20° C and relative humidity of 50 % until an illumination of 10 and 20 megalux hours was reached.
- the density loss was measured with a densitometer Spectrolino ® .
- the percent density loss of initial density gives an indication of the light stability of the dyes on the printed recording sheet.
- the optical density of the coloured square patches was measured with a Spectrolino ® densitometer. Afterwards, the printed samples were stored for a predetermined time (for example 48 hours) in an ozone chamber, model 903 (available from Satra/Hampden, Great Britain) at a temperature of 30° C, a relative humidity of the air of 50 % and an ozone concentration of 1 ppm at a velocity of the circulating, ozone containing air of 13 mm/s. After storage, the samples were re-measured. The density differences of these two measurements, expressed as per cent of the initial density, are an indication of the amount of dye loss due to the exposure to ozone.
- the dyes (2), (3), (13), (14) and (18) have a considerably better stability in comparison to the black dyes (I), (II), (III) and (IV) forming the state of the art.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Claims (11)
- Schwarze Disazofarbstoffe der allgemeinen Formel (V)M ein Wasserstoffatom, ein Natriumatom, ein Potassiumatom, ein Lithiumatom, ein Ammoniumkation oder ein aliphatisches Ammoniumkation mit 4 identischen Substituenten mit 1 bis 4 Kohlenstoffatomen repräsentiert,A ein Rest der Formel (VI) istwobei R1 ein Wasserstoffatom, ein Halogenatom, eine Sulfonsäuregruppe oder eine Nitrogruppe repräsentiert,R2 ein Wasserstoffatom, eine Carbonsäuregruppe, eine Sulfonsäuregruppe, eine Hydroxygruppe oder eine Nitrogruppe repräsentiert,R3 ein Wasserstoffatom, ein Halogenatom, eine Nitrilgruppe, eine Carbonsäuregruppe, eine Sulfonsäuregruppe, eine Nitrogruppe, eine Alkylgrupppe mit 1 bis 4 Kohlenstoffatomen, eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen substituiert durch 1 bis 3 Halogenatome, eine Estergruppe mit 1 bis 4 Kohlenstoffatomen, eine Alkoxylgruppe mit 1 bis 4 Kohlenstoffatomen, eine unsubstituierte oder substituierte heterozyklische Gruppe, eine Sulfonamidgruppe, eine Sulfonylgruppe, eine Sulfoestergruppe mit 1 bis 4 Kohlenstoffatomen oder eine Alkylamidgruppe mit 1 bis 4 Kohlenstoffatomen präsenitert,R4 ein Wasserstoffatom, ein Halogenatom, eine Carbonsäuregruppe, eine Sulfonsäuregruppe, eine Nitrogruppe, eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen, eine Alkoxylgruppe mit 1 bis 4 Kohlenstoffatomen, eine Sulfonamidgruppe, eine Sulfonylgruppe, eine Sulfoestergruppe mit 1 bis 4 Kohlenstoffatomen oder eine Alkylamidgruppe mit 1 bis 4 Kohlenstoffatomen präsenitert,R5 ein Wasserstoffatom, ein Halogenatom, ein Nitrilgruppe, eine Nitrogruppe, eine Hydroxygruppe, eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen oder eine Alkylamidgruppe mit 1 bis 4 Kohlenstoffatomen repräsentiert,B ein Rest der Formel (VI) istR6 ein Wasserstoffatom, ein Halogenatom, eine Sulfonsäuregruppe oder eine Nitrogruppe repräsentiert,R7 ein Wasserstoffatom, eine Carbonsäuregruppe, eine Sulfonsäuregruppe, eine Hydroxygruppe oder eine Nitrogruppe repräsentiert,R8 ein Wasserstoffatom, ein Halogenatom, eine Nitrilgruppe, eine Carbonsäuregruppe, eine Nitrogruppe, eine Alkylgrupppe mit 1 bis 4 Kohlenstoffatomen, eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen substituiert durch 1 bis 3 Halogenatome, eine Estergruppe mit 1 bis 4 Kohlenstoffatomen, eine Alkoxylgruppe mit 1 bis 4 Kohlenstoffatomen, eine unsubstituierte oder substituierte heterozyklische Gruppe, eine Sulfonamidgruppe, eine Sulfonylgruppe, eine Sulfoestergruppe mit 1 bis 4 Kohlenstoffatomen oder eine Alkylamidgruppe mit 1 bis 4 Kohlenstoffatomen repräsentiert,R9 ein Wasserstoffatom, ein Halogenatom, eine Carbonsäuregruppe, eine Sulfonsäuregruppe, eine Nitrogruppe, eine Aminogruppe, eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen, eine Alkoxylgruppe mit 1 bis 4 Kohlenstoffatomen, eine Sulfonamidgruppe, eine Sulfonylgruppe, eine Sulfoestergruppe mit 1 bis 4 Kohlenstoffatomen oder eine Alkylamidgruppe mit 1 bis 4 Kohlenstoffatomen repräsentiert,R10 ein Wasserstoffatom, ein Halogenatom, ein Nitrilgruppe, eine Sulfonsäuregruppe, eine Nitrogruppe, eine Hydroxygruppe, eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen oder eine Alkylamidgruppe mit 1 bis 4 Kohlenstoffatomen repräsentiertund
B wenigstens eine Sulfonsäuregruppe aufweist. - Schwarze Disazofarbstoffe der allgemeinen Formel (V) nach Anspruch 1, dadurch gekennzeichnet, dassM wie in Anspruch 1 definiert ist,R1 ein Wasserstoffatom, ein Halogenatom oder eine Sulfonsäuregruppe repräsentiert;R2 ein Wasserstoffatom oder eine Carbonsäuregruppe repräsentiert;R3 ein Wasserstoffatom, eine Nitrogruppe oder eine Sulfonsäuregruppe präsentiert;R4 ein Wasserstoffatom, ein Halogenatom, eine Sulfonsäuregruppe, eine Carbonsäuregruppe, eine Nitrogruppe oder eine Alkylamidgruppe mit 1 bis 4 Kohlenstoffatomen repräsentiert;R5 ein Wasserstoffatom oder eine Nitrilgruppe repräsentiert,R6 ein Wasserstoffatom, eine Nitrogruppe oder eine Sulfonsäuregruppe repräsentiert;R7 ein Wasserstoffatom oder eine Carbonsäuregruppe repräsentiert;R8 ein Wasserstoffatom, eine Sulfonsäuregruppe oder eine Nitrogruppe repräsentiert;R9 ein Wasserstoffatom, eine Sulfonsäuregruppe, eine Carbonsäuregruppe oder eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen repräsentiert undR10 ein Wasserstoffatom oder eine Sulfonsäuregruppe repräsentiert.
- Schwarze Disazofarbstoffe der allgemeinen Formel (V) nach den Ansprüchen 1 und 2, dadurch gekennzeichnet, dassM wie in Anspruch 1 definiert ist,R2 wie in Anspruch 2 definiert istR1 ein Wasserstoffatom oder eine Sulfonsäuregruppe repräsentiert;R3 ein Wasserstoffatom oder eine Sulfonsäuregruppe repräsentiert;R4 ein Wasserstoffatom, eine Sulfonsäuregruppe oder eine Carbonsäuregruppe repräsentiert;R5 ein Wasserstoffatom repräsentiert,R6 ein Wasserstoffatom oder eine Sulfonsäuregruppe repräsentiert;R7 ein Wasserstoffatom repräsentiert;R8 ein Wasserstoffatom oder eine Nitrogruppe repräsentiert;R9 ein Wasserstoffatom, eine Sulfonsäuregruppe oder eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen repräsentiert undR10 ein Wasserstoffatom repräsentiert.
- Schwarze Disazofarbstoffe der allgemeinen Formel (V) nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet, dass die Sulfogruppe an der Position γ ist.
- Verfahren zur Präparation von schwarzen Disazofarbstoffen der allgemeinen Formel (V) nach Anspruch 1, dadurch gekennzeichnet, dass
in einem ersten Schritt
ein Amin der allgemeinen Formel (XII),
in einem wässrigen anorganischen Säuremedium bei einer Temperatur zwischen -5°C und 15°C diazotiert ist und an der Komponente der Formel (XIV)
in einem zweiten Schritt
ein Amin der allgemeinen Formel (XV),
in einem anorganischen Säuremedium bei einer Temperatur zwischen -5°C und 15°C diazotiert ist und mit dem Reaktionsprodukt aus Schritt 1 bei einem leicht basischen bis basischen pH-Wert, der zwischen 8 und 10 liegt, gebunden ist. - Verfahren zum Aufzeichnen von Text und Abbildungen auf Aufzeichnungsblättern und zum Färben und Bedrucken natürlicher oder synthetischer Fasermaterialien, nanoporöser Materialien, Leder und Aluminium durch das Aufbringen von schwarzen Disazofarbstoffen oder einer Mischung aus schwarzen Disazofarbstoffen nach einem oder mehreren der Ansprüche 1 bis 4.
- Flüssigfarbstoffpräparate mit wenigstens einem schwarzen Disazofarbstoff oder einer Mischung aus schwarzen Disazofarbstoffen nach einem der Ansprüche 1 bis 4.
- Aufzeichnungsflüssigkeiten zum Tintenstrahldrucken und für Schreibutensilien mit wenigstens einem schwarzen Disazofarbstoff oder einer Mischung aus schwarzen Disazofarbstoffen nach einem oder mehreren der Ansprüche 1 bis 4.
- Aufzeichnungsflüssigkeiten zum Tintenstrahldrucken und für Schreibutensilien mit wenigstens einem schwarzen Disazofarbstoff oder einer Mischung aus schwarzen Disazofarbstoffen nach einem oder mehreren der Ansprüche 1 bis 4 und zusätzlich einem oder mehreren anderen Farbstoffen.
- Aufzeichnungsflüssigkeiten zum Tintenstrahldrucken und für Schreibutensilien nach Anspruch 9, dadurch gekennzeichnet, dass der zusätzliche Farbstoff oder die Farbstoffe gelbe Farbstoffe sind.
- Aufzeichnungsflüssigkeiten zum Tintenstrahldrucken und für Schreibutensilien nach Anspruch 10, dadurch gekennzeichnet, dass der gelbe Farbstoff oder die gelben Farbstoffe ausgewählt sind aus der Gruppe, die C.I. Direct Yellow 86, C.I. Direct Yellow 98, C.I. Direct Yellow 132, C.I. Direct Yellow 142, C.I. Direct Yellow 173, C.I. Acid Yellow 23, C.I. Reactive Yellow 3, das hydrolysierte Derivat von C.I. Reactive Yellow 3, C. I. Yellow 85, das hydrolysierte Derivat von C.I. Reactive Yellow 85, C.I. Yellow 95 oder das hydrolysierte Derivat von C.I. Yellow 95 umfasst.
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EP10187827.0A EP2441805B1 (de) | 2010-10-16 | 2010-10-16 | Schwarze Disazofarbstoffe, ihre Herstellung sowie Verwendung |
AU2011226772A AU2011226772B2 (en) | 2010-10-16 | 2011-09-20 | Black disazo dyes, their preparation and use |
CN201110308167.0A CN102453342B (zh) | 2010-10-16 | 2011-10-12 | 黑色双偶氮染料、其制备及用途 |
KR1020110104000A KR101314804B1 (ko) | 2010-10-16 | 2011-10-12 | 흑색 디스아조 염료, 그 제조방법 및 용도 |
US13/274,741 US8834620B2 (en) | 2010-10-16 | 2011-10-17 | Black disazo dyes, their preparation and use |
JP2011227801A JP6084356B2 (ja) | 2010-10-16 | 2011-10-17 | 黒色ジスアゾ色素、黒色ジスアゾ色素の製造方法、染色および印刷する方法、液体色素調製物、及びインクジェット印刷または筆記具用の記録液体 |
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EP10187827.0A EP2441805B1 (de) | 2010-10-16 | 2010-10-16 | Schwarze Disazofarbstoffe, ihre Herstellung sowie Verwendung |
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EP (1) | EP2441805B1 (de) |
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EP2641940A1 (de) * | 2012-03-22 | 2013-09-25 | ILFORD Imaging Switzerland GmbH | Wasserlösliche und wasserfeste Farbstoffe für Tintenstrahldruck |
WO2015144419A1 (en) * | 2014-03-28 | 2015-10-01 | Memjet Technology Limited | Ink formulations for improving printhead lifetime |
EP3583173B1 (de) * | 2017-04-13 | 2020-11-04 | Memjet Technology Limited | Tintenformulierungen mit niedriger toxizität und verbesserter druckkopflebensdauer |
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US3923778A (en) * | 1969-11-12 | 1975-12-02 | Ciba Geigy Ag | Disazo dyestuffs containing the {60 :{62 -dichloro- or {60 :{62 -dibromopropionylamino group |
JPS594451B2 (ja) | 1978-07-21 | 1984-01-30 | 住友化学工業株式会社 | ジスアゾ染料の製法 |
JPS6036193B2 (ja) | 1980-04-21 | 1985-08-19 | 富士写真フイルム株式会社 | インクジエツト印刷用水性インキ |
JPS5736692A (en) | 1980-08-14 | 1982-02-27 | Fuji Photo Film Co Ltd | Sheet for ink jet recording |
DE3327713A1 (de) | 1983-07-29 | 1985-02-07 | Hoechst Ag, 6230 Frankfurt | Wasserloesliche disazoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe |
DE3340590A1 (de) * | 1983-11-10 | 1985-05-23 | Bayer Ag, 5090 Leverkusen | Polyazoreaktivfarbstoffe |
US5250121A (en) | 1991-09-26 | 1993-10-05 | Canon Kabushiki Kaisha | Ink-jet textile printing ink and ink-jet textile printing process |
US5748208A (en) | 1992-05-22 | 1998-05-05 | Seiko Epson Corporation | Color ink jet recording method |
GB9217964D0 (en) * | 1992-08-24 | 1992-10-07 | Ici Plc | Compound |
DE19523245A1 (de) | 1995-06-27 | 1997-01-02 | Bayer Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
US5935309A (en) | 1996-10-31 | 1999-08-10 | Hewlett-Packard Company | Ink-jet inks for improved print quality |
US5997623A (en) | 1997-06-16 | 1999-12-07 | Xerox Corporation | Ink jet inks comprising anti-curl agents and printing processes |
GB9816780D0 (en) * | 1998-07-31 | 1998-09-30 | Basf Ag | Reactive dyes containing a linkage |
US6171349B1 (en) * | 1999-01-20 | 2001-01-09 | Everlight Usa, Inc. | Reactive dye composition |
US6503308B2 (en) | 2000-12-20 | 2003-01-07 | Hewlett-Packard Company | Black ink compositions for inkjet printing |
JP4677403B2 (ja) * | 2004-04-09 | 2011-04-27 | 日本化薬株式会社 | アゾ化合物、インク組成物及び着色体 |
US20070227388A1 (en) * | 2004-05-10 | 2007-10-04 | Hiroaki Ohno | Tetrakisazo Compound, Coloring Matter for Recording, Ink Composition and Colored Article |
CN100362056C (zh) | 2005-02-05 | 2008-01-16 | 明德国际仓储贸易(上海)有限公司 | 黑色墨水染料组成物 |
EP1889882A1 (de) * | 2005-06-09 | 2008-02-20 | Nippon Kayaku Kabushiki Kaisha | Azo-verbindung, tintenzusammensetzung, aufzeichnungsverfahren und gefärbtes material |
CN100413927C (zh) | 2005-09-05 | 2008-08-27 | 明德国际仓储贸易(上海)有限公司 | 双偶氮染料化合物及其应用 |
CN101235219B (zh) * | 2007-02-01 | 2010-09-08 | 明德国际仓储贸易(上海)有限公司 | 应用于纺织品数字印染的黑色染料组成物及墨水组成物 |
CN101289579B (zh) * | 2007-04-16 | 2011-03-30 | 明德国际仓储贸易(上海)有限公司 | 黑色染料组成物及黑色墨水组成物 |
CN101362864A (zh) * | 2008-10-06 | 2009-02-11 | 丽源(内蒙古)科技有限公司 | 一种复合活性黑染料 |
TWI444437B (zh) * | 2010-06-18 | 2014-07-11 | Everlight Chem Ind Corp | 藍色、紅色及黃色染料化合物及所組成之黑色墨水組成物 |
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US8834620B2 (en) | 2014-09-16 |
EP2441805A1 (de) | 2012-04-18 |
KR20120047197A (ko) | 2012-05-11 |
JP2012087301A (ja) | 2012-05-10 |
AU2011226772A1 (en) | 2012-05-03 |
US20120090503A1 (en) | 2012-04-19 |
KR101314804B1 (ko) | 2013-10-10 |
JP6084356B2 (ja) | 2017-02-22 |
AU2011226772B2 (en) | 2013-02-07 |
CN102453342B (zh) | 2016-06-08 |
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